FD Ep. 74 Jon Tucker

200 Employees, One Founder, and a Whole Lot of AI

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The Fastest Way to Close a Deal? Start with a Plan.

Most founders start fundraising without a real strategy, then wonder why it takes forever.
Our Capital Strategy Assessment gives you a precise path to capital (debt, equity, or M&A) and the right people to talk to.

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The AI Playbook: How to Build More With Less with Jon Tucker

This week on Fundraising Demystified, I sit down with Jon Tucker, founder of HelpFlow, who bootstrapped his company to 200+ employees and is now using AI to outcompete, automate, and scale faster than ever.

What you can expect:

• 01:30 - AI’s impact on customer service & workforce reduction
• 04:00 - The Importance of Evaluating AI Performance
• 07:15 - How AI enables business efficiency and scalability
• 12:45 - AI’s role in startup growth and venture capital trends
• 18:30 - AI workflow automation & AI-assisted coding
• 24:00 - Future of AI: Chief AI Officers, automation, and scaling
• 28:30 - Boardy AI and next-gen AI-powered networking

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ABOUT JON TUCKER

Jon Tucker is the CEO at Help Flow. Over the past decade, he’s managed remote teams and faced the frustrations of micromanaging every detail—an experience that drove him to embrace AI for smarter delegation.

Through HelpFlow’s “smart staff” model and their proprietary GuideLayer AI, Jon transforms traditional virtual assistants into high-value, autonomous team members. His goal? Free founders from busywork so they can scale faster and focus on what truly matters. Ready to see how AI can change the way you work? Try the AI at HelpFlow.com/demo-ai-video.

Connect with Jon Tucker: 

• Website
• LinkedIn

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Let's Connect:

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